1,2,4-triazole based compounds that can be used as insecticides or acaricides and processes

Abstract

3-(Substituted aryl)-5-{substituted aryl-(alkynyl-aryl)}-[1,2,4]- triazole compounds are useful as insecticides and acaricides. New synthetic procedures and intermediates for preparing the compounds, pesticide compositions containing the compounds, and methods of controlling insects and mites using the compounds are also provided.

We claim:  
     
       1. A compound of the formula (1)                    
       wherein 
       Ar is phenyl, substituted phenyl, pyridyl, substituted pyridyl, or lower alkyl;  
       R 1  is lower alkyl, cycloalkyl, or substituted phenyl;  
       Q is thienyl, substituted thienyl, pyridyl, or substituted pyridyl;  
       R 2  is selected from H, lower alkyl, lower alkenyl, pyridyl, substituted pyridyl, pyrimidyl, substituted pyrimidyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, thienyl, substituted thienyl, —(CH 2 ) m R 3 , —CH═CHR 3 , —C≡CR 3 , —CH 2 OR 3 , —CH 2 SR 3 , —CH 2 NR 3 R 3 , —OCH 2 R 3 ,                    
       R 3  is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;  
       m is 1 or 2;  
       n is an integer from 2 to 6;  
       or a phytologically acceptable acid addition salt thereof. 
     
     
       2. A compound of  claim 1  wherein Ar is a group of the formula                    
       wherein R 4  and R 5  are independently H, Cl, or F. 
     
     
       3. A compound of  claim 2  wherein R 4  and R 5  are independently F or Cl. 
     
     
       4. A compound of  claim 2  wherein R 4  and R 5  are both F. 
     
     
       5. A compound of  claim 2  wherein R 4  is F and R 5  is Cl. 
     
     
       6. A compound of of  claim 1  wherein Ar is a group of the formula                    
       wherein R 4  and R 5  are independently H, Cl, or F. 
     
     
       7. A compound of  claim 6  wherein R 4  and R 5  are independently F or Cl. 
     
     
       8. A compound of  claim 2  wherein R 4  and R 5  are both Cl. 
     
     
       9. A compound of  claim 1  wherein Ar is lower alkyl. 
     
     
       10. A compound of  claim 1  wherein Q is a thiophene or substituted thiophene. 
     
     
       11. A Compound of  claim 1  wherein Q is a pyridyl or substituted pyridyl. 
     
     
       12. A compound of  claim 1  wherein R 1  is methyl, ethyl, hydrogen, cyclohexyl, or substituted phenyl. 
     
     
       13. A compound of  claim 1  wherein R 2  is a phenyl or substituted phenyl. 
     
     
       14. A compound of  claim 1  wherein R 2  is a thiophene or substituted thiophene. 
     
     
       15. A compound of  claim 1  wherein R 2  is a trimethyl silyl, lower alkyl (ethyl, propyl, n-butyl, t-butyl), or lower alkenyl (propenyl). 
     
     
       16. A composition for controlling insects or mites which comprises a compound of  claim 1  in combination with a phytologically-acceptable carrier. 
     
     
       17. A method of controlling insects or mites which comprises applying to a locus where control is desired an insect- or mite-inactivating amount of a compound of  claim 1 . 
     
     
       18. A method of controlling beet armyworm which comprises applying to a locus where control is desired a beet armyworm inactivating amount of a compound of  claim 1 . 
     
     
       19. A method of controlling tobacco budworm which comprises applying to a locus where control is desired a tobacco budworm inactivating amount of a compound of  claim 1 . 
     
     
       20. A method of controlling cabbage looper which comprises applying to a locus where control is desired a cabbage looper inactivating amount of a compound of  claim 1 . 
     
     
       21. A method of controlling aphids which comprises applying to a locus where control is desired an aphid inactivating amount of a compound of  claim 1 . 
     
     
       22. A method of controlling whitefly which comprises applying to a locus where control is desired a whitefly inactivating amount of a compound of  claim 1 . 
     
     
       23. A method of controlling mites which comprises applying to a locus where control is desired a mite-inactivating amount of a compound of  claim 1 . 
     
     
       24. A method of protecting a plant from aphids, mites, or insects which comprises treating plant seed prior to planting it, treating soil where plant seed is to be planted, or treating soil at the roots of a plant after it is planted, with an effective amount of a compound of  claim 1 . 
     
     
       25. A process for preparing a compound of formula (1)                    
       wherein  
       Ar is phenyl, substituted phenyl, pyridyl, substituted pyridyl, or lower alkyl;  
       R 1  is lower alkyl, cycloalkyl, or substituted phenyl;  
       Q is thienyl, substituted thienyl, pyridyl, or substituted pyridyl;  
       R 2  is selected from H, lower alkyl, lower alkenyl, pyridyl, substituted pyridyl, pyrimidyl, substituted pyrimidyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, thienyl, substituted thienyl, —(CH 2 ) m R 3 , —CH═CHR 3 , —C≡CR 3 , —CH 2 OR 3 , —CH 2 SR 3 , —CH 2 NR 3 R 3 , —OCH 2 R 3 ,                    
       R 3  is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;  
       m is 1 or 2;  
       n is an integer from 2 to 6;  
       which comprises reacting a compound of formula                    
       wherein Ar, Q, and R 1  are as defined above,  
       with an appropriately substituted aryl iodide or aryl bromide of R 2  under palladium catalysis.  
     
     
       26. A process for preparing a compound of formula (1)                    
       wherein  
       Ar is phenyl, substituted phenyl, pyridyl, substituted pyridyl, or lower alkyl;  
       R 1  is lower alkyl, cycloalkyl, or substituted phenyl;  
       Q is thienyl, substituted thienyl, pyridyl, or substituted pyridyl;  
       R 2  is selected from H, lower alkyl, lower alkenyl, pyridyl, substituted pyridyl, pyrimidyl, substituted pyrimidyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, thienyl, substituted thienyl, —(CH 2 ) m R 3 , —CH═CHR 3 , —C≡CR 3 , —CH 2 OR 3 , —CH 2 SR 3 , —CH 2 NR 3 R 3 , —OCH 2 R 3 ,                    
       R 3  is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;  
       m is 1 or 2;  
       n is an integer from 2 to 6;;  
       which comprises reacting a compound of formula                    
       wherein Ar, Q, and R 1  are as defined above, and X is Br or I with a terminal alkyne of R 2  of formula (1) in  claim 1  under palladium catalysis.  
     
     
       27. A compound of the formula                    
       wherein  
       Ar is phenyl, substituted phenyl, pyridyl, substituted pyridyl, or lower alkyl;  
       R 1  is lower alkyl, cycloalkyl, or substituted phenyl;  
       Q is thienyl, substituted thienyl, pyridyl, or substituted pyridyl.